Can you post some more images of the interior of the textured-surface box (and/or describe it)? This might help me try to date the it. As it is, I can't quite tell what the setup is for holding a watch.

For the one with the red bottom interior, I'm guessing 1933-1935. I have an Elgin ladies' model from 1933, complete with the original bracelet, that came in its original box, whose general style is similar to yours. It's also a long, skinny one, but the setup for the bracelet provides little tabs to which the bracelet is attached, extended at length. (I'll try to post an image later.)

Thanks for the replies Magpie. I will put some additional pictures up. My two boxes appear to accommodate strapped watches as there is a slot in each of them where one side of the strap is inserted (and hidden) and then the watch is folded back with the watch case and strap side with the buckle displayed. This I thought indicated the boxes housed men's watches. My pics will better illustrate this than my narrative here.

Thanks for the compliment about my watch and its box! I've found that sometimes one can get a good idea of the date of an Elgin box for a men's model from some details of box construction for a ladies' model, so I figured you'd like to see it for comparison with yours.

And thanks for the description of the interior of the mystery box -- I thought that was likely how the insert was set up (and thus for a men's model) but I wanted to make sure. It's apparently an early one of that type, likely from about 1926. (I have a related ladies' box coming and will post a picture once it gets here. I'll have more details for you then.)

Here are additional pics of the boxes. The smaller one is the oldest and is likely as Magpie suggests, 20s. The larger one is still early 30s. Magpie, your box looked like it had some metal on the rim, is that right? Would the use of metal mean later vintage than my larger one? If so, the larger of my two is likely slightly older than yours.

With the larger box you can see in the indentation and shape from the watch case itself. The tabs secure the buckle end of the strap to the box.